Wednesday Wisdom

The wickedest city in the New World

This is what is left of Port Royal in Jamaica. At its peak, Port Royal compared to Boston Massachusetts and Charleston, South Carolina in terms of population and commerce. The city’s history is short but colorful and also is a lesson in ethics when it comes to sovereign legality.

After Christopher Columbus returned from his first voyage in 1492, both Spain and Portugal claimed rights to newly discovered lands. To avoid conflict, they negotiated a treaty that effectively divided the non-European world between them. Christopher Columbus’s second trip to the new world was one of conquest. Columbus’s second voyage began on September 24, 1493. He left Spain with a massive fleet of 17 ships and roughly 1,200–1,500 people including soldiers, priests, farmers, officials, and settlers. This was a dramatic expansion from the Nina, Pinta and Santa Maria of the first voyage. Spain’s goal was no longer exploration but colonization, conversion, and securing imperial claims. The voyage landed in Jamacia but for the next 160 years it was largely ignored and only used as supply base because of the abundance of fresh water from the blue mountains., Instead, they concentrated on Hispaniola and Cuba due to their natural riches including gold and sugar. These islands became Spain's crown jewels creating tremendous wealth for European nation. The Caribbean islands became a steppingstone for Spain’s imperial conquest of South and Central America.

In 1655, English Lord Protector of England, Scotland and Ireland instituted the "Western Design", a campaign to seize some of Spain's lucrative new world territories. In May 1655, Admiral Penn and General Robert Venables commanded an English force of about 7,000 troops and 30 ships that invaded and captured Spanish Jamaica. The original target was Hispaniola, but that attack failed, to salvage the mission, Venables pushed to attack Jamaica. Penn personally led the landing at Caguaya Bay, near modern Kingston, where Spanish defenses were weak, and the island fell quickly. Jamaica became an English colony and remained so until 1962.

Port Royal was one of the wealthiest and most notorious cities in the Caribbean during the 17th century. Under English rule, it became a hub for privateers which are government authorized pirates who attacked Spanish shipping. The English government benefited from this arrangement because privateers (pirates) helped weaken Spain and brought wealth into Jamaica and Port Royal. It also started escalation of warfare between the countries that lasted for centuries. At the same time, Port Royal developed a reputation for corruption, smuggling, drunkenness, gambling, and prostitution.

On June 17th, 1692, in the same time it takes to boil water, Port Royal fell into the sea. The destruction of Port Royal in 1692 is often used as a moral or ethical lesson about lawlessness. When a massive earthquake struck, much of the city sank into the sea and thousands perished. Many contemporaries, especially clergy, interpreted the disaster as divine punishment for the city's perceived wickedness. They saw it as evidence that a society built on vice and government sanctioned predation would eventually face judgment. From a modern historical perspective, however, the earthquake was a natural geological event, not a moral verdict. Historians generally avoid claiming that natural disasters happen because of ethical failures.

In that sense, Port Royal can be viewed as a case study in the dangers of a government profiting from activities that would otherwise be considered criminal. The lesson is less the earthquake was punishment and more that states who normalize unethical conduct may eventually face serious consequences either political, economic, or social.

It's also interesting to compare Port Royal with later examples where governments tacitly supported activities that were profitable but ethically questionable, such as state sponsored privateering, monopolies, corruption networks, or even certain forms of regulatory capture. The ethical question remains the same, does the government approval make an activity morally acceptable, or merely legally permissible? Philosophers from Plato to John Locke would argue that legality and morality are not always the same thing.

2026-this question is more important than ever

The story still offers an ethical and political lesson that governments may gain short term benefits from tolerating or encouraging illegal or unethical activities. The line between legality and morality can become blurred when the state itself authorizes questionable behavior. Systems built on corruption, exploitation, or lawlessness can become unstable and vulnerable to collapse.

Political ethics have been studied and argued since ancient Greece. In Politics, Aristotle distinguished between "correct" governments, which serve the common good, and "deviant" governments, which serve rulers' private interests. For Aristotle, corruption occurs when public office becomes a tool for personal enrichment. Marcus Tullius Cicero the Roman statesman, orator and philosopher repeatedly criticized Roman officials who exploited public office for private gain. He argued that government officials are trustees of the people and violate natural law when they use power for personal benefit. Niccolo Machiavelli is often thought as endorsing ruthless politics in The Prince, however, Machiavelli was deeply concerned with corruption. In Discourses on Livy, he argued that republics decay when citizens and leaders place private interests above civic virtue.

The philosophers of the Enlightenment and the US Constitution had strong opinions on governments, democracy and concentration of power. John Locke argued that government exists through the consent of the governed. When rulers use public power for private advantage rather than protecting rights, they break the social contract and may be legitimately resisted. Jean- Jacques Rousseau believed governments often become captured by wealthy interests and cease representing the "general will." He warned that inequality and private influence can corrupt public institutions. Montesquieu in The Spirit of the Laws argued that concentrated power breeds corruption. His solution was separation of powers and institutional checks to prevent officials from exploiting their positions.

John Dalberg-Acton (1834–1902), commonly known as Lord Acton, was an English parliamentarian, historian, political thinker, and moral philosopher who may have summed it up the best. In a letter to fellow historian Mandell Creighton, Lord Acton wrote the famous line;

“Power tends to corrupt, and absolute power corrupts absolutely”.


And now you know...

Philosophy is the art of thinking, the building block of progress that shapes critical thinking across economics, ethics, religion, and science.

METAPHYSICS: Literally, the term metaphysics means ‘beyond the physical.’ Typically, this is the branch that most people think of when they picture philosophy. In metaphysics, the goal is to answer the what and how questions in life. Who are we, and what are time and space?

LOGIC: The study of reasoning. Much like metaphysics, understanding logic helps to understand and appreciate how we perceive the rest of our world. More than that, it provides a foundation for which to build and interpret arguments and analyses.

ETHICS: The study of morality, right and wrong, good and evil. Ethics tackles difficult conversations by adding weight to actions and decisions. Politics takes ethics to a larger scale, applying it to a group (or groups) of people. Political philosophers study political governments, laws, justice, authority, rights, liberty, ethics, and much more.

AESTHETICS: What is beautiful? Philosophers try to understand, qualify, and quantify what makes art what it is. Aesthetics also takes a deeper look at the artwork itself, trying to understand the meaning behind it, both art as a whole and art on an individual level. A question an aesthetics philosopher would seek to address is whether or not beauty truly is in the eye of the beholder.

EPISTEMOLOGY: This is the study and understanding of knowledge. The main question is how do we know? We can question the limitations of logic, how comprehension works, and the ability (or perception) to be certain.